Team Free Will Walks Into A Bar
by BooksAndNetflix
Summary: Dean, Cas, Sam and Charlie walk into a bar. There's fluff and there's bets. Purple nurples and Destiel just because I can. Post season 8. Cas is human, Dean admitted his feelings, Sam knew it all along and Charlie had helped them figure it out along the way. But this is all after that at a bar in some no name town. Read and review(:


"Dean, see that girl over there?" Charlie says, passing a beer across the table to him while nodding over his shoulder at the said girl.

"Yeah, what, you got the hots for her? Want me to wingman?"

"No, better then that. I wanna bet. Whoever gets her number buys the next round and gets bragging rights."

"There are two obvious problems with your plans, first, how do you know she'll be into either of us," Dean asked without giving her a chance to respond. "And two, I'm with Cas, remember. I may be new to the whole 'committed relationship' thing but not hitting on other people seems pretty basic to me."

Just then Cas slid into the booth next to Dean and Sam next to Charlie. "What is basic Dean?"

"Yeah Dean, what's basic?" Sam said while smirking, he had heard the tail end of the conversation and was always amused when his brother was forced to explain certain things to a very clueless, and newly human, Cas.

"It's basic to not hit on other people when you already have another someone," he told Cas, giving him a quick welcome kiss on the cheek. "Which is why I'm not gonna take you up on that bet Charlie."

"I think you're just scared you're gonna lose," Sam told Dean.

"Bitch."

"Jerk."

"Boys, boys, play nice," Charlie interrupted. She turned to Castiel, "Would it bother you if Dean took me up on a bet to see who could pick up that girl sitting at the bar."

"It would not bother me; I know that he does not have any affection for her and that it is just a game."

"See? Man up Winchester," Charlie said.

"That doesn't answer my first question, how do you know she'll give her number to either of us?"

"What, tall guys and red heads?"

Sam snickered. "You know what I mean."

"Call it a sixth sense."

"You saw her flirting with some guys and girls didn't you."

Charlie replied without missing a beat. "Yeah, sixth sense, observation, same thing, you don't have either."

"C'mon, you're knocking me down left and right. I don't know whether to be proud or insulted!"

"Both, both is good."

"So, ladies first?"

"My pleasure," Charlie said, gesturing for Sam to move so she could get up behind him. She squared her shoulders and then relaxed them. As she walked toward the girl at the bar, she flashed a smile and wink over her shoulder where Dean was not very subtly watching the events about to unfold, and Castiel and Sam looked on with indifference.

Charlie sat on the chair and ordered a drink, probably a purple nurple if Dean had to guess, she had an obsession with that drink. Then she turned toward the girl, slightly on the short side, with high cheekbones that Charlie was most likely internally swooning over. She had dark hair and vaguely reminded Dean of a female version of some detective on a show that Sammy geeks out over.

The ex-queen of Moondore flipped her hair over her shoulder and beamed at the detective look-a-like. She mouthed something and the woman laughed and cracked a smile, putting a flirtatious hand on Charlie's forearm.

"She could be pulling one over you, who says femSherlock over there isn't strictly into girls?" Sam stated. "Oh she's gonna make you look like a fool!" Sam said, letting out a short laugh at the prospect of Dean looking like an idiot.

Sherlock, duh, that's who she looks like. "Charlie is fair, she would not make a barter with Dean if she was not sure they both had a chance at winning."

"I'm telling her that you doubted her honor, she'll whip you a new one Sammy."

"Why am I going to beat Sam?"

"He questioned your honor, saying that you picked a female that did not like the company of men." Cas informed in such a serious manner that Dean just had to lean over and kiss him.

"Guys really? At the table?"

"Shove it Samantha."

"Do any of you want to know the outcome of me and cutie Sherlock girl over there?" Charlie asked, looking amused and victorious. She held up one of those square napkins with a phone number scrawled across it. Next to it was the outline of pink lips and 'call me.'

"Showoff," grumbled Dean, but moved to get up the same. "Wish me luck?" he asked Castiel.

"I do not see how luck has anything to do with getting a phone numb—" Dean cut him off with another quick kiss before walking away, going through the same routine as Charlie when she stood up, minus the wink.

"Hey," Dean coughed, a little uncomfortable with flirting knowing his angel was twenty feet away. "You come here often?"

"Never heard that one before," the girl said, turning away from Dean.

"Can I at least get a name?"

"Cassandra, but my friends call me Cassie."

Of course, Dean mentally groaned. Why did she have to have that name? "So Cassie—"

"I said my friends call me Cassie, you, are not my friend."

"Ok, sorry, it's just I'm a little nervous."

"Big muscle, tough guy and you're . . . nervous?" Cassie asked, a little shocked.

"It's just been awhile, that's all."

"Oh I'm sorry, I didn't know. Did you lose someone?"

"Something like that," Dean replied vaguely.

"What was her name?"

"Huh? Oh, her name was . . . Mary." It technically wasn't a lie; he did lose her, just not in the way Cassie was insinuating.

"Oh."

"So . . . Can I buy you a drink? Get your number?"

"Uh, sorry, you're not really my type."

"Are you not into—"

"The big muscle-y type," Cassie replied before Dean could get out the word 'guys.'

Now it was Dean's turn to say, "Oh."

He stood up dejectedly. "You'll find someone," she smiled at him.

"Yeah," he said, glancing back at his angel and smiling too. "I'm sure I will."

Dean walked back to the table and shrugged, which made Charlie pump her fist into the air. "The queen wins again!"

"Who really wins?" Dean asked, stealing a kiss from his angel.

"Why did you lose?" Sam asked.

"I wasn't too interested, I mean, her name was Cassie for fucks sake. That was weird." Dean replied.

"Yeah, yeah, excuses. Cut the chit chat and cough up the cash for the next round of purple nurples." Charlie said eagerly. Seriously, she drank those like Dean ate pie. Dean handed over the money and she skipped to the bar, making a detour to Cassie on the way. Dean ducked his head to kiss Cas again, earning a groan from Sam as he went up to the bar to help Charlie with the drinks.

"Yeah," Dean said, "I definitely think I'm the overall winner."

* * *

**Yeah, so this thought kinda popped up in my head and I wrote it down. Sorry for any mistakes, no beta and such. Hoped you like it and hoped I stayed pretty true to the characters. Review your thoughts, I'd love to hear them!**


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